CH311568A - Process for the production of a new basic substituted fatty acid amide. - Google Patents
Process for the production of a new basic substituted fatty acid amide.Info
- Publication number
- CH311568A CH311568A CH311568DA CH311568A CH 311568 A CH311568 A CH 311568A CH 311568D A CH311568D A CH 311568DA CH 311568 A CH311568 A CH 311568A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl
- fatty acid
- methyl
- production
- acid amide
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäureamides. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen basiseh substituierten Fettsäureamides, wel- ebes dadureh gekennzeichnet ist, dass man auf eine Verbindung der Formel
EMI0001.0008
eine Verbindung der Formel
EMI0001.0010
in welchen Formeln X und Y reaktionsfähige, bei der Reaktion sich abspaltende Reste be deuten, einwirken lässt.
Als Verbindungen der Formel I kommen für einen Umsatz beispielsweise in Frage: Das freie Amin (Y = H), aber auch dessen Salze, wie beispielsweise das Hydrochlorid oder das Sulfat.
Als Verbindungen der Formel II kommen beispielsweise in Frage: 2-DTethyl-piperidino- essigsäure selbst und ihre reaktionsfähigen funktionellen Derivate wie ihre Halogenide, ihre Ester, ihre Anhydride, beispielsweise die reinen und auch die gemischten Anhydride mit. Pllosphorsäure, Schwefelsäure und Koh- leilsallre usf.
Man kann beispielsweise N-[2-(2'-lIethyl- phenoxy)-ätllyl-] ]-N-methylamin oder auch ein Salz desselben in Gegenwart eines für diese Zwecke geeigneten wasserabspaltenden Mittels wie Phosphorpentoxyd, Phosphoroxy- chlorid usf. mit 2-Methyl-piperidino-essig- säure behandeln.
Weiter kann man auch N-[2-(2'-Methyl- phenoxy)-äthyl-1]-N-methylamin bzw. ein Salz desselben mit einem 2-Methyl-piperidino-essig- säurehalogenid (bzw. einem Salz eines sol chen) oder einem Anhydrid zur Reaktion bringen.
Es ist weiterhin auch möglich, N-[2-(2'- Methyl-phenoxy)-äthyl-1]-N-methylamin mit einem 2 - Methyl - piperidino - essigsäureester, vorzugsweise einem Arylester, bei erhöhter Temperatur zu acylieren.
Das auf diese Weise erhaltene N-[2-(2'- Methyl-phenoxy)-äthyl-1 ] -1\,T-methyl-2"-ineth@Tl- piperidino-acetamid bildet ein farbloses, unter 0,2 mm bei 190-192 siedendes öl.
Das neue Amid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden. <I>Beispiel:</I> 16g N-[2-(2'-Methyl-phenoxy)-äthyl-1]-N- methylamin in Benzol werden mit einer Mi- sehung von 20 g 2-Methyl-piperidino-essig- säurechlorid-hydrochlorid und 20 g Triäthyl- amin erwärmt.
Anschliessend wird das gebil dete Triäthylaminhydrochlorid durch Aus schütteln mit Wasser entfernt, die Benzol lösung nach dem Trocknen verdampft imd der Rückstand im Hochvakulun destilliert. Man erhält so in guter Ausbeute das N-[2-(2' Methyl-phenoxy) - äthyl-1 ] -N-methyl- 2"-me- thyl-piperidino-acetamid, welches ein unter 0,2 mm bei 190-192 siedendes farbloses Öl darstellt.
Die Reaktion kann auch ohne Verdün- nungs- und Kondensationsmittel durchgeführt werden, indem man beispielsweise das N-[2- (2'-1@Tethyl-phenoxy)-äthyl-l ] -N-methylamin mit 2-1lethyl-piperidino-essigsäureehlorid-hy- drochlorid trocken erhitzt, anschliessend die Reaktionsmasse mit Wasser verdünnt und in üblicher Weise aufarbeitet.
Process for the production of a new basic substituted fatty acid amide. The subject matter of the present patent is a process for the production of a new basic substituted fatty acid amide, which is characterized by the fact that a compound of the formula
EMI0001.0008
a compound of the formula
EMI0001.0010
in which formulas X and Y are reactive residues that are split off during the reaction.
Compounds of the formula I that can be used for conversion are, for example: The free amine (Y = H), but also its salts, such as the hydrochloride or the sulfate, for example.
Examples of possible compounds of the formula II are: 2-DTethylpiperidinoacetic acid itself and its reactive functional derivatives such as its halides, its esters, its anhydrides, for example the pure and also the mixed anhydrides. Plloosphoric acid, sulfuric acid and carbon sallre etc.
For example, N- [2- (2'-lethylphenoxy) -ätllyl-]] -N-methylamine or a salt thereof in the presence of a dehydrating agent suitable for this purpose, such as phosphorus pentoxide, phosphorus oxychloride, etc., with 2- Treat methyl piperidino acetic acid.
It is also possible to use N- [2- (2'-methylphenoxy) ethyl-1] -N-methylamine or a salt thereof with a 2-methyl-piperidino-acetic acid halide (or a salt of one of these) ) or an anhydride to react.
It is also possible to acylate N- [2- (2'-methyl-phenoxy) -ethyl-1] -N-methylamine with a 2-methyl-piperidino-acetic acid ester, preferably an aryl ester, at elevated temperature.
The N- [2- (2'-methyl-phenoxy) -ethyl-1] -1 \, T-methyl-2 "-ineth @ Tl-piperidino-acetamide obtained in this way forms a colorless, less than 0.2 mm at 190-192 boiling oil.
The new amide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. <I> Example: </I> 16 g of N- [2- (2'-methyl-phenoxy) -ethyl-1] -N-methylamine in benzene are mixed with 20 g of 2-methyl-piperidino-acetic acid - heated acid chloride hydrochloride and 20 g triethylamine.
The formed triethylamine hydrochloride is then removed by shaking with water, the benzene solution is evaporated after drying and the residue is distilled in a high vacuum. The N- [2- (2 'methyl-phenoxy) -ethyl-1] -N-methyl-2 "-methyl-piperidino-acetamide, which has a lower than 0.2 mm at 190- 192 represents boiling colorless oil.
The reaction can also be carried out without a diluent and condensing agent, for example by mixing N- [2- (2'-1 @ methyl-phenoxy) -ethyl-1] -N-methylamine with 2-1-methyl-piperidino-acetic acid chloride -Hydrochloride heated dry, then the reaction mass diluted with water and worked up in the usual way.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH311568T | 1952-06-08 | ||
CH306201T | 1955-03-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH311568A true CH311568A (en) | 1955-11-30 |
Family
ID=25735095
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH311568D CH311568A (en) | 1952-06-08 | 1952-06-08 | Process for the production of a new basic substituted fatty acid amide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH311568A (en) |
-
1952
- 1952-06-08 CH CH311568D patent/CH311568A/en unknown
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CH311568A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311558A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311567A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311565A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311563A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311562A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311571A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311569A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311552A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311557A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311577A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311564A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311575A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311570A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311573A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311561A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311566A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311560A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311559A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311576A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311554A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311556A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311572A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311553A (en) | Process for the production of a new basic substituted fatty acid amide. | |
CH311555A (en) | Process for the production of a new basic substituted fatty acid amide. |